The Confidence Crisis: Why Women Feel Unwanted and Men Feel Undateable

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“Men are cowards. Why are they so afraid to ask girls out?” she asked as she stirred her coffee. “Guys are like parking spaces. All the good ones are taken.”

The funny thing is that I had talked with a man who went to her church who felt the same way.

“Women won’t say ‘yes’ to going out unless they already know and like you,” he said. “They won’t give you the chance to get to know them. Girls are like parking spaces. All the good ones are taken.”

Are all the great guys taken? Are there really no amazing single women left? Could it be that the problem is that our perceptions are shaped by our confidence?   In some ways, the world reflects back to us what we are feeling. When we feel happy, we tend to notice things that will make us happy. When we are sad, it is easy to focus on the bad news.

One of the fun things about writing Courtship in Crisis is that I have been able to interview wonderful single men and women around the world. I can tell you there are a ton of of great ones left.

Here is what I think the problem is.

Why Men Feel Undateable

Relationships require a lot of courage, particularly for men who have to take the initial risks. Which begs the question: how do you become confident enough to ask a girl out?

I can tell you where confidence doesn’t come from: it doesn’t come from giving trophies to losers. I think the self confidence movement has it wrong on this point. In Little League, we all kept score in our heads since our moms didn’t want us to feel bad about losing. We weren’t fooled when they purposefully confused success and failure.

Real confidence comes from past success when failure was likely. Success without possible failure is like food without flavor: it has all the substance, but none of the enjoyment.

Also, there are some lessons than only failure can teach.

Courtship teaches that you should not enter into a relationship until you are “ready to get married.” But can someone ever really be ready for marriage? I don’t know a single married couple who when looking back says they were really ready. Typically they describe marriage as being like jumping off a cliff into a cold lake. They thought they were ready, but when they hit the water the cold and excitement knocked their breath away.

If we are not careful, “readiness” can be a bit like a carrot on a stick that one can never really attain.

Courtship advocates prohibit young men from spending one-on-one time with young women and then are shocked (shocked!!!!) when these young men become adults and lack the confidence or competence to pursue single women.

This would be like prohibiting football players from playing football in high school and then wondering why they are bad at college football. College players hit a lot harder. To play at that level, you need the kind of confidence and competence that comes only from years of practice.

This is one of the beautiful things about Traditional Dating. By encouraging young people to go on platonic dates while discouraging them from going steady, we give them a chance to build their confidence and competence. It takes practice to woo a woman. It takes time to get past the cooties stage of girl-guy relationships.

If a guy asks a girl out for ice cream, it boosts the girl’s confidence. If the girl says “yes”, this boosts the guy’s confidence. When some girls say “no”, it makes the “yeses” mean all the more.

There is a kind of mother who does all she can to protect her sons from failure. They are then often surprised to see that all their sons want to do is play video games. I think the chance of failure is part of why video games appeal to young men so much.  When you fail in those games, the game rubs the failure in your face. Often you see your body on the ground while the screen pans around it with the text “You lose!” flashing in big letters.

When the game says “You win”, it means something real because failure is a real option. The game designers have found a way for success to feel more real in the game than in a real world where well-meaning mothers shelter their sons from failure.

Going back to the sports analogy, not all football players are good enough to play for the Texas Longhorns. But anyone who wants to play football can find a league that fits. It may be the UMHB Crusaders, an intramural team, or a church pickup game. God made marriage as an institution for everyone, not just the rich and beautiful. Or, put another way, there is parking space for everyone.

Why Women Feel Unwanted

While researching for Courtship in Crisis, I have had the chance to interview a lot of women. While every woman is unique, there are some things that many women have in common.

For instance, many women need to hear that they are beautiful.

When a woman goes a long time without hearing how pretty she is, she can start to think that she is unattractive. The less attractive a woman feels, the less she smiles and the less she takes care of herself. This can create a vicious cycle that becomes a self-fulfilling prophecy since men are more attracted to women who smile and take care of themselves.

In many courtship communities, men don’t feel like they can compliment women because that would be considered flirting, which is strictly taboo. The thinking is that for a man to compliment a woman he must first be committed to her. So, most feedback women get on their appearance is from other women.

Men and women don’t find the same things attractive. In my experience, women have a fairly narrow view of what they consider beautiful in other women. Depending on the community, this standard can be unhealthily high.

Men, on the other hand, have a predisposition to find women attractive. I think God put this in the male psyche to propagate the species. Furthermore, each man has a certain type of woman that he finds most attractive and that “type” varies greatly from man to man.

The good news for women is that most young men find most young women attractive. I agree with the old Southern saying that “there is a lid for every pot.”  Although I think it is fair to say that some lids fit more pots than others.

Who do you think will be more confident? The woman who is home waiting for Prince Charming to fight his way past her Dragon Father? Or the woman who is going on frequent dates and hearing how pretty she is from multiple guys?

Having talked with a lot of courtship-minded women, I can tell you few of them feel beautiful. They are trapped in a system that isolates them from any form of “flirting” or encouragement from guys. The feedback they get from their families could also make them feel unworthy of attention.

A lot of conservatives blame “that ugly feeling” on the media. Indeed, it is true that the media has an unreasonably high standard for beauty. At the end of all the makeup and Photoshop, the models themselves can’t live up to their own pictures.

But, I don’t think media is fully to blame for why women feel unattractive.

A woman who feels loved and cherished rarely feels ugly because of the media. The same is true for the woman who is being pursued by several men. The pursued woman is less vulnerable to the media’s influence. It is the lonely woman who looks upon the media’s impossible standard and is tempted to despair.

We can’t do much about the messages the media puts out. But we can encourage young men to encourage young women.

Single women get verbal affirmation more frequently in Traditional Dating than in Courtship. The platonic, low commitment dates of Traditional Dating give young women a frequent opportunity to dress up and hear that they are beautiful. This verbal encouragement from the young man on the other side of the table helps boost their confidence.

The Confidence Crisis


The Confidence Crisis

Our insecurities can form a vicious cycle of men not pursuing women, making women feel ugly and unwanted. A woman who feels unwanted is more likely to reject men because the man’s words will sound insincere in her ears. “How could he really like me? He must be lying.” So they reject making men feel less confident making them less likely to pursue women and so on.

So, some men lack the confidence to ask the women out, which makes the women feel that they are not attractive to men. Women who feel unattractive are more likely to reject men. Getting rejected makes men less likely to pursue. The women’s hiding then makes men feel even less confident, resulting in a vicious cycle.

Courtship encourages singles to “spend time in groups”, not realizing that most of the group interactions are segregated. There are few girls at the game night and few men at the Bible study. It is almost as if there is a huge wedge of insecurity separating the men from the women.

The joke in my area is that you know you are at a “homeschool party” when the guys and girls chat in mostly separate groups. Even at parties of 20-somethings, when the sexes start to cluster someone asks, “Is this a homeschool party?”

The courtship community has become saturated in fear:

  • Fear of failure.
  • Fear of divorce.
  • Fear of temptation.
  • Fear of rejection.

The fear can become so choking that it is hard to breathe, much less to thrive. The parents are afraid. The pastors are afraid. The singles are afraid.

I have some good news. In the words of an old VeggieTales song: “God is bigger than boogie man.” God is bigger than our failures, our rejections, our temptations, and our divorces. He has provided a way out of the confidence crisis.

Seven Steps to Find Your Courage

The purpose of this post is not just to point out the problems in the status quo, but to provide some practical suggestions.

No one is born courageous. Most babies cry at loud noises and most children are afraid of the dark. The good news is that anyone can find courage. There are few things more powerful in this world than someone who, while facing their fear, chooses to act anyway.

Here are seven steps to help you become a more courageous person.

Step 1: Be Afraid

Boldness is the absence of fear. You either have it or you don’t. The best way to be bold is to be ignorant of the risk. Courage, on the other hand, is action in the face of fear. Courage is doing the right thing despite possessing a vivid understanding of the danger. So the first step to finding courage is identifying the fear. Without fear you can’t show courage.

Fear focuses the mind, heightens the senses, and boosts energy. Your body starts to change as you experience fear. Courage redirects that energy and points it in a positive direction.

As a professional public speaker, I learned that my best talks happened when I was terrified. As my old speech coach told me, “Good public speaking is not about getting rid of the butterflies. It is about getting them to fly in formation.” There is a level of energy I can achieve on stage only when jittery with fear.

What do you fear? Does the idea of asking that cute girl at church out for ice cream make you want to vomit? Does the thought of spending time alone with a guy at a public place make you want to run away and hide? Are you terrified of repeating the painful mistakes of the past?

These fears intend to cripple you into inaction. But they don’t have to. They can empower you to do something you would otherwise never be able to do. But the first step is to acknowledge the fear and see it as something separate from you as a person.

Step 2: Find Out Who You Are

If you are a follower of Christ, you have been given a new identity (2 Cor 5:17). You are now a child of light (Ephesians 5:8). You are born again as a son or daughter of the King of Kings (Romans 8:15-16).  God has given you a new name (Revelation 2:17). He has taken your garments of wickedness and replaced them with robes of righteousness (Galatians 3:26-27).

You are not a coward. The Bible tells us “The wicked flee though no one pursues, but the righteous are as bold as a lion.” Proverbs 28:1 NIV

Knowing who you are in Christ can change your perspective on your fear. Yes, a heavenly perspective on your problems can make them look small in light of the universe, but it is more than that. True confidence can’t come from others. It can only come from God.

A good example of the power of identity can be found in the Bible’s book of Judges. For years the Israelites had been attacked by the Midianites. The Midianites were so cruel that the Israelites started hiding in caves anytime the Midianites came around. The worst part was that the Midianites took all the food they could get their hands on. What they didn’t take they burned until the Israelites were starving.

God, choosing to intervene, sent an angel to speak to a man who was hiding at the bottom of a winepress. What did the angel say to this man? Did he say “Climb out of that winepress you coward, God wants you to save Israel.” No! He said, “Mighty hero, the Lord is with you!” The very first thing the angel gave to Gideon was a new name, a new title. He was no longer Gideon the coward hiding in a hole. He was Gideon the mighty hero.

Once Gideon got his new identity, the winepress was no longer the place for him because mighty heroes don’t hide in holes. Gideon went on to have a series of adventures, culminating in a surprise attack where he and 300 men ambushed the Midianite army. God blessed Gideon’s courage and caused the massive army to fight itself in panic. Gideon rescued Israel and led it into a season of peace and prosperity. You can read about Gideon and his adventures in Judges 6-8.

Ask God to tell you who you are. As He gives you your new identity, don’t be surprised if your courage starts to grow.

Step 3: Change Your Self-Talk

When it comes to finding our confidence, we are often our own worst enemies. What do you tell yourself when you look in the mirror? Is it words of encouragement and affirmation? If you are like most people, you are much meaner to yourself than you are to anyone else.

Many of us were taught to guard against pride by putting ourselves down. But this is not true humility. As C.S. Lewis said, “True humility is not thinking less of yourself. It is thinking of yourself less.” False humility (rejecting compliments, dismissing strengths, and emphasizing weaknesses) can actually be a form of pride.

For example, when we reject someone’s compliment, we are saying “My view of me is more important than your view of me.” Which is a somewhat arrogant way to look humble.

If anyone were as verbally abusive to one of my family members as I am to myself, there would be a fight. I wouldn’t let anyone talk to my family that way and yet I put up with my own terrible self-talk.  Also, people who hate themselves tend to judge others more harshly. So the meaner I am to myself, the meaner I tend to be towards others.  It is hard to love my neighbor as myself when I treat myself so badly.

In 2 Corinthians 10, Paul talks about taking our thoughts captive and forcing them to be obedient to Christ. This idea that we have control over our own thoughts is a powerful principle.

Deciding in our minds that we believe what God says about us more than what we think about ourselves could be called “repentance.” Repentance literally means to change your thinking. In some ways, changing our thinking is the hardest kind of repentance. I can believe what God says about others, but can I believe what He says about me?

Gideon had to change his thinking when the angel called him a mighty hero while he was still hiding.  He had to repent from thinking of himself as a coward. This change in his self-talk required faith. And at first his faith was very small. He didn’t go straight from hiding to ambushing the Midianites. He had a series of adventures first. Each adventure helped grow his faith. God patiently helped Gideon adjust to his new identity.

There is a powerful moment in the Lord of the Rings when The Fellowship is being chased by a giant fire demon called a Balrog. Finally, Gandalf, the leader of the party, turns around and faces the monster.

What happens next is one of my favorite passages in the book:

“You cannot pass,” he said. The orcs stood still, and a dead silence fell. “I am a servant of the Secret Fire, wielder of the flame of Anor. You cannot pass. The dark fire will not avail you, flame of Udûn. Go back to the Shadow! You cannot pass.”

Gandalf knew exactly what he was facing. He had every reason to be afraid. But he also knew who he was. He spoke his identity to himself as much as to the monster. He had the courage to face the monster and save his friends.

Step 4: Suit Up

On the football field one of the things that gives the players courage is the fact that they are wearing pads and a helmet. But, perhaps more importantly, they are also wearing a uniform. The uniform says “I am on a team. The other guys in this uniform have my back. Together we are going to do what none of us could do alone.” Around every highlight reel on ESPN is a team of guys blocking and making the big play possible.

As Christians, God clothes us in robes of righteousness and places us within His team, The Body of Christ. So we suit up in a spiritual sense when we put on our uniform and embrace our role within The Body. He doesn’t just surround us with fellow warriors. He also gives us heavenly pads and a helmet to keep us safe in a dangerous world.

Surrounding yourself with fellow believers who encourage and look out for you can boost your confidence. If you are shy, having a good friend who can act as a wingman to make introductions for you can be very helpful. You could say that when Jesus talked about the “Friend of the Bridegroom”, he was talking about a wingman.

In one sense, John the Baptist was a wingman helping introduce the people to Jesus. The key to being a good wingman is to know how to gracefully leave the conversation once things get started. There is a moment in the conversation when the wingman must decrease so the friend can increase.

We can also suit up in a literal sense. There is an ancient Latin saying, Vestus virum reddit. Or, “the clothes make the man.” How you dress signals to your body how to act. I saw this first hand in speech and debate. It was amazing how differently young men behaved when they were wearing suits and ties. If you want to get in the mood for exercise, put on your exercise clothes. Somehow the clothes change your mood.

Clothes are a tangible way to signal both to yourself and to others what you think about yourself. If you see yourself as a slob, you will dress like a slob. If you see yourself as an attractive and confident person, your clothes will reflect that.

Suiting up is not just about clothing. It is about how you carry yourself.

Stand tall. Roll your shoulders back. Look the world in the face with a smile. You may be surprised to find the world smiling back at you. Lift your chin and let the confidence flow through you.  You are not a beggar that must keep his eyes on the ground. You are a child of God.  The more you act like it, the more you will feel it.

Step 5: Take Risks

The first time I sang in a choir, I was terribly nervous. I was sweaty and could hardly get the words out.  But, ten years later, I could sing confidently without a hint of nerves. What changed? I sang in hundreds of choir performances. I took risks by auditioning. That practice and those risks gave me confidence to try bigger challenges in the future. The things I used to find nerve-racking as a child no longer scared me as a teenager.

When my family started the Austin Rhetoric Club, we found that a lot of students would join the club only to leave before delivering a single speech. So my dad changed the rules so that everyone gave a speech their very first day at the club, even if it was just to introduce themselves. The first speech was always the hardest and once students got that out of the way, it was a lot easier to come back.

For the students who put off or avoided giving that first speech, it grew into a monster in their minds. They wanted more and more training before they felt ready to give the speech. The more training they received, the more they realized they didn’t know, until finally they gave up and stopped coming.

Some things can be learned only by doing. You can’t learn how to play the piano in a book. The only way to learn how to play the piano is to first play badly while you learn how to play it well.  Interacting with the opposite sex is same way. We are tempted to believe that the longer we wait, the easier it will become. This is like putting off piano practice in hopes that we will play better by procrastinating.

The reality is the longer we put off dating, the scarier it becomes in our mind. So we grab another relationship book and hope to get more ready. Books are not a replacement for practice. The sooner you work through the awkwardness of cooties, the sooner you can find your confidence.

Men, the more you ask girls out, the easier it will be.  The longer you put it off, the more of a monster it becomes in your mind.  So if you are a guy, ask a girl out for lunch.

Women, if the guy is a Christian and he asks you to dinner, say “yes.” Give him a chance one-on-one to woo you. Who knows, you might actually enjoy it! 🙂

Step 6: Fail and Try Again

There is a kind of courage that can be forged only through failure. Someone who has never failed has never found the limit of their abilities. They are likely far more able than they realize.

If we never fail, the fear of failure can grow like a splinter in the mind. A man who has never experienced failure can only imagine how it feels like to fail. It is easy for the imagination of such a man to run away with him.

As I have said in an earlier post, failure is like hot coffee. It is too hot to touch, but not too hot to drink. It is once you fail, and have learned to take the heat of it, that it starts to lose its power over you. If all you do is touch the hot coffee, you can start to believe that it is undrinkable.

Failure can also bring you closer to God. You never know God loves you when you fail, till you fail and feel God’s love. Once you experience the love of God in the midst of your failure there is no stopping you.

Step 7: Experience God’s Love

The Bible tells us in 1 John 4 that “Such love has no fear, because perfect love expels all fear.”  While it is true that a mother will do courageous acts to save the child she loves, I think there is more to this verse than that.  God’s perfect love for us casts out our fear.

Do you feel deep down that God loves you? He loves you so much he sent his Son to die so that you could be reconciled to him. You can feel God’s love for you. There is an old saying that a man with an experience is not at the mercy of a man with an argument. Once you personally experience the love of God you will never be the same.

God wants to shower you in love in such a way that you can experience it. All you have to do is ask Him.

From Vicious Cycle to Virtuous Cycle

The Confidence Cycle

As men start to overcome their fear and pursue women, women will begin to feel more beautiful, which will, in fact, make them more beautiful. This greater beauty will encourage more men to pursue them and so on.

All it takes to start the change is a simple compliment, and invitation to coffee, or a “yes” to lunch.  You can do it!

What do you think?



Thomas Umstattd Jr. is the author of Courtship in Crisis, the former head of PracticalCourtship.com, and co-founder of the Austin Rhetoric Club, a homeschool speech and debate club in Austin, Texas. He is a professional speaker and CEO of Author Media. He sits on the board of directors for several nonprofits, including the Texas Alliance for Life.

Please note: I reserve the right to delete comments that are offensive or off-topic.

7 thoughts on “The Confidence Crisis: Why Women Feel Unwanted and Men Feel Undateable

  1. Another reason women might say no to dates out of insecurity is for fear for saying something stupid, coming off as high maintenance, making awkward conversation, or a number of other fears unrelated to their appearance. In other words, there can be just as much fear and risk in the accepting of a date as there is in the asking for a date. And that brings me to the question of women asking men on dates, but maybe that’s a discussion for another blog post.

  2. Women like the girl in the opening sentence, who are wondering why men are so afraid to ask girls out, need to be a little more introspective and should consider how many men they themselves have turned down. (I’ve often wondered if single, lonely women ever consider this.) I think these types of problem pertain mainly to Western Christian culture (at least in America). My personal experience as a single Christian man has been, unfortunately, that it is relatively easy to ask out a non-Christian girl, but most Christian girls are so bound up with fear or a holier than thou attitude that it’s next to impossible to get near enough to even begin to get to know her.

  3. One of the best articles I’ve read on the subject. Thank you for the balance and honesty you bring to the discussion.

  4. Great! Seems slightly repetitive at times (i’m thinking the section “Why women feel unwanted), but really great points.

  5. I absolutely agree. Grew up with the courship but so discouraging when I looked around at beautiful, single, young ladies who had never been courted! Figured I had no chance since they were all so gorgeous . . . 🙂 So I dated, but behind my parents back. Big disaster. Long story short, I don’t even entirely regret it because I’m married now with a toddler! Love being married. Whereas my older sister is still single :(. Recently I decided that I WANT my kids to date! It is good experience, it is fun, and I think that when kids are allowed to go on healthy dates, they are less likely to “mess up” like I did. Parents are scared to let kids date because they don’t want mess ups, but I think preventing mess ups should come by instilling confidence in our kids. Thank you for writing about this topic!

  6. The vast majority of women now are extremely self-centered and materialistic. They only see men as a financial instruments and will trade up in a heartbeat for a better one (80% of divorces filed by women).

    Men are beginning to realise women are simply a bad investment and are giving up on dating or approaching them.

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